Cheap Flights from Chicago Midway to Philadelphia

Compare Chicago Midway to Philadelphia flight deals

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Flight deals from Chicago Midway to Philadelphia

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Philadelphia? If you want to travel next month, return fares start from $321. Find the lowest prices on one-way and return tickets right here.

Philadelphia.$286 per passenger.Departing Sat, 5 Sep, returning Tue, 8 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 5 Sep, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Tue, 8 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $286, select.

Philadelphia.$313 per passenger.Departing Thu, 17 Sep, returning Sat, 19 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 17 Sep, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 19 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $313, select.

Philadelphia.$313 per passenger.Departing Sat, 3 Oct, returning Wed, 7 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 3 Oct, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Wed, 7 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $313, select.

Philadelphia.$321 per passenger.Departing Wed, 12 Aug, returning Mon, 17 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 12 Aug, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Mon, 17 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $321, select.

Philadelphia.$325 per passenger.Departing Tue, 25 Aug, returning Tue, 1 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 25 Aug, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $325, select.

Philadelphia.$347 per passenger.Departing Mon, 28 Sep, returning Mon, 5 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 28 Sep, arriving in Philadelphia International.Inbound indirect flight with Southwest Airlines, departs from Philadelphia International on Mon, 5 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $347, select.

Philadelphia.$410 per passenger.Departing Sat, 14 Nov, returning Wed, 18 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 14 Nov, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Wed, 18 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $410, select.

Philadelphia.$411 per passenger.Departing Thu, 29 Oct, returning Mon, 2 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 29 Oct, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Mon, 2 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $411, select.

Philadelphia.$439 per passenger.Departing Mon, 28 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 28 Sep, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $439, select.

Philadelphia.$439 per passenger.Departing Sat, 14 Nov, returning Wed, 18 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 14 Nov, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Wed, 18 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $439, select.

Philadelphia.$439 per passenger.Departing Mon, 10 Aug, returning Thu, 13 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 10 Aug, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Thu, 13 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $439, select.

Philadelphia.$440 per passenger.Departing Wed, 18 Nov, returning Tue, 1 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 18 Nov, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Tue, 1 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $440, select.

Philadelphia.$440 per passenger.Departing Sat, 29 Aug, returning Sat, 5 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 29 Aug, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Sat, 5 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $440, select.

Philadelphia.$469 per passenger.Departing Fri, 30 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 30 Oct, arriving in Philadelphia International.Inbound direct flight with Southwest Airlines departs from Philadelphia International on Mon, 2 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $469, select.

Philadelphia.$496 per passenger.Departing Tue, 21 Jul, returning Tue, 28 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 21 Jul, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Tue, 28 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $496, select.

Philadelphia.$496 per passenger.Departing Wed, 29 Jul, returning Sat, 1 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 29 Jul, arriving in Philadelphia International.Inbound indirect flight with Frontier Airlines, departs from Philadelphia International on Sat, 1 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $496, select.

Find the cheapest month to fly from Chicago Midway to Philadelphia

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Philadelphia flights are currently cheapest in September.

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Direct flights from Chicago Midway to Philadelphia

Alternative Chicago Midway to Philadelphia routes

Looking for the cheapest, fastest or easiest route from Chicago Midway to Philadelphia? You could fly into the following airports instead.

Chicago to Philadelphia: Flight information

The things to know before you go.

Cheapest flight found	$286
Cheapest month to fly	September
Average flight time	1 hr, 58 mins
Most popular airline	Southwest Airlines
Average flights per week	33

Finding cheap flights from Chicago Midway to Philadelphia: Frequently asked questions

How many airports are there in Philadelphia?

There are 5 airports in Philadelphia: Philadelphia International, Philadelphia Trenton-Mercer, Greater Wilmington, Atlantic City International, and Allentown.

How much are return flights from Chicago Midway to Philadelphia?

The best price we found for a return flight from Chicago Midway to Philadelphia is $286. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Chicago Midway to Philadelphia?

1 hour and 58 minutes is the average flight time from Chicago Midway to Philadelphia.

Which airlines fly direct from Chicago Midway to Philadelphia?

Southwest Airlines flies direct from Chicago Midway to Philadelphia.

How many flights are there a week from Chicago Midway to Philadelphia?

As of July 2026, there are 33 flights per week flying from Chicago Midway to Philadelphia.

When is the cheapest time to fly from Chicago Midway to Philadelphia?

The cheapest month to fly from Chicago Midway to Philadelphia is usually September.

Which is the cheapest airport to fly into in Philadelphia?

If you're flying from Chicago Midway Airport, the cheapest airport near Philadelphia is Philadelphia International – which is 11.2 km away from the centre of Philadelphia. We've found flights into this airport from $286.

Which upcoming date is cheapest to fly from Chicago Midway Airport to Philadelphia on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Philadelphia on Saturday, 5 September 2026.

Can I get a direct flight from Chicago Midway Airport to Philadelphia?

Yes – the average flight time is 1 hour and 58 minutes.

How can I get the best flight deal from Chicago Midway Airport to Philadelphia?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Philadelphia but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Philadelphia?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Philadelphia is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Philadelphia?

In July, the average temperature is usually around 24°C. July is typically the warmest month in Philadelphia, when it usually averages around 30°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is July.

Which is the cheapest airline to fly from Chicago Midway Airport to Philadelphia with?

Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Philadelphia.

Flying from Chicago Midway International Airport (MDW) to Philadelphia: what you need to know

Expect to be travelling for 2 hours 10 minutes. That's the average time for a direct flight from Chicago Midway International Airport to Philadelphia.
The timezone in Philadelphia is UTC-5. The city is one hour ahead of Chicago, where Chicago Midway International Airport is located.
With 22 weekly flights between the two airports, Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL) is the most popular route. Southwest Airlines operates the earliest flight at 05:50. If you prefer to get more out of your day before you fly, the latest flight from MDW to PHL is with Southwest Airlines at 21:55.
For a relaxed start to your MDW to Philadelphia flight, leave enough time to check in and find your gate. Turning up two hours ahead of international departures and one hour before domestic flights is the general travel rule.
During popular months such as July, it's wise to get to the airport earlier than usual. Plan to arrive two hours before a domestic departure and four hours ahead for an international flight whenever you're flying during a peak period in general.
Direct Chicago Midway International Airport to Philadelphia tickets are available for booking. Philadelphia International Airport (PHL) is where you'll arrive.
Take to the skies with Southwest Airlines. This well-known carrier offers direct flights from Chicago Midway International Airport to Philadelphia.
MDW is around 14 kilometres from central Chicago. If you're ride-sharing, driving or catching a taxi from the centre, it'll take you 25 minutes or so to get there, depending on traffic conditions. If you're using public transport, expect the journey time to be around 30 minutes.
Booked an early flight from Chicago Midway International Airport to Philadelphia? Avoid the last-minute rush to the terminal (and enjoy a little extra shut-eye) by choosing one of these hotels close to MDW:
Of the departures from Chicago Midway International Airport, 76% arrive on time at their destination.
MDW's address is 5700 South Cicero.

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Philadelphia

$142 is currently the lowest price for a one-way Chicago Midway International Airport to Philadelphia flight. A return plane ticket starts from $286. These fares may change depending on availability.
Booking in advance is often the key to securing a cheap flight from MDW to Philadelphia. Fares tend to rise as demand increases, so the nearer you get to departure, the more you'll likely pay.
The 'Whole month' tool will show you the cheapest tickets from Chicago Midway International Airport to Philadelphia across the entire month. It's a good way to snap up a bargain if your dates are flexible.
Locking in a cheap flight from MDW to Philadelphia is easy with Price Alerts. All you need to do is create one of these automatic notifications and we'll let you know as soon as a new discount appears.
Save on your flight from Chicago Midway International Airport to Philadelphia with the help of our filters. Choose your preferred times, number of stops and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Philadelphia

Philadelphia International Airport (PHL)

The distance from Philadelphia International Airport (PHL) to central Philadelphia is roughly 18 kilometres. It takes about 20 minutes to reach the centre driving.
It typically takes 30 minutes when travelling by public transport.
Consider booking a hotel near PHL if you're coming in on a late flight from Chicago Midway International Airport to Philadelphia. Check in to one of these options and skip the long transfer:
Lock in the best possible rate by reserving your vehicle from Philadelphia International Airport about three weeks in advance of your flight from MDW to Philadelphia.
PHL is located at 8500 Essington Ave.

Trenton-Mercer Airport (TTN)

Central Philadelphia is located around 48 kilometres from Trenton-Mercer Airport (TTN). Once your flight from Chicago Midway International Airport to Philadelphia has hit the runway and you've navigated your way to arrivals, the drive should take about 40 minutes.
If you travel by public transport, you'll reach the centre in 1 hour 35 minutes or so.
Hang up the 'Do not disturb' sign and rest at a hotel close to TTN. Here are a few options where you can kick back after your MDW to Philadelphia flight:
Avoid last-minute price surges. Booking your ride four weeks ahead of your arrival at TTN can get you a lower rate.
Trenton-Mercer Airport can be found at Scotch Road, Terminal Building.

Best time to go to Philadelphia

July is the most popular month for flights from Chicago Midway International Airport to Philadelphia. To avoid the crowds, visit Philadelphia in December.
When booking your Chicago Midway International Airport to Philadelphia plane ticket, think about the type of weather you enjoy. July is the warmest month in Philadelphia, with temperatures ranging from 18ºC to 32ºC.
Search for cheap tickets from MDW to Philadelphia in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -7ºC and 9ºC on average.

More about Philadelphia

After booking your flight from Chicago Midway International Airport to Philadelphia, choose a hotel that puts you right where the action is. Make one of these accommodation options your base for exploring Philadelphia:
There are so many things to discover in this city it can be difficult to know where to start. Liberty Bell, Independence Hall and Philadelphia Museum of Art are leading attractions which should feature on any good Philadelphia itinerary.

Explore more of the United States

New York is just one of the many places in the United States waiting to be discovered once you've seen the sights of Philadelphia. Around 129 kilometres away to the northeast, well-known attractions include Central Park, Statue of Liberty and Metropolitan Museum of Art.
Boston is another well-known destination in the United States and is around 434 kilometres northeast of Philadelphia. No journey is complete without dropping by Museum of Fine Arts Boston, Freedom Trail and USS Constitution Museum.